The specularity map is built in a similar way to the bump map. Start with a base layer that is a greyscaled version of the original bmp so you can line other layers up accurately against it. Rather than thinking about how raised or sunken objects are you need to thing about how shiny they would be. Darker shades on the spec map file are duller on the skin, lighter shades are shinier.
In the case of the F6F shown above, the base blue paint was semi gloss but this tended to dull down with age. The white paint was duller so I've made the markings a slightly darker shade to represent this. The paint chips shown on the prop are shiny and so are much lighter, as is the glass on the light covers and bulbs. The paint chipped rivets are also lighter. Tyres and panel lines are dull so they are darker and so on. Use seperate layers for each material, its much easier to edit later on that way.
Note that shiny materials, as on bare metal skins, tend to show up the bump mapping effects to a greater extent than dull ones. So you may want to tone down the bump mapping effects a bit on these skins relative to one with dull camouflage paint.
The maximum shininess of the skin is controlled by the bumpmat.txt file. This is very similar to the material.txt file and does the same job but only when the player selects bump mapping. Here are the two files from the P-47D-25:
Material.txt
0.361,0.361,0.361,Ambient
0.639,0.639,0.639,Diffuse
0.000,0.000,0.000,Emissive
0.450,0.450,0.450,Specular
10.000,Power
Bumpmap.txt
0.361,0.361,0.361,Ambient
0.639,0.639,0.639,Diffuse
0.000,0.000,0.000,Emissive
1.000,1.000,1.000,Specular
10.000,Power
The only difference between them is the Specular line. In the case of the material.txt file the specularity of the whole skin would be 0.450, about midway between fully matt 0.000 and fully shiny 1.000. On the bumpmat.txt file this line is set to full gloss 1.000. However this is only the maximum shinyiness any part of the skin can be. The only parts of the skin that will be this shiny are those that are painted pure white on the specularity map. Anything that is a shade of grey will be less shiny than this. In short just take your original material file and make the fourth line: 1.000,1.000,1.000,Specular for the bumpmat file.